There was a time that I had 3 boats (I guess 4 if you consider the dinghy). It was wonderful because I bought them in a series which helped me learn and get each boat to a point that I could sail and enjoy it. At the time, I was living on one of the boats, so I was always close to the others for basic maintenance and repairs. They all served different purposes. One was our home (45' motor yacht), one was a condo for visiting family and a rental to a friend for a year (38' sailboat). The last was for sailing around (23' sailboat) and keeping my skills up while learning from the much more experienced sailors that lived in the same marina. None of the boats were in spectacular condition when I got them or when I sold them, but they were made better in my care. The sailboats were in rough condition when I bought them, both requiring new propulsion, 1 inboard and 1 outboard, the motor yacht was pretty sorted but needed new water heaters and upgraded black water plumbing because we wanted to use our fresh water tanks rather than seawater for flushing. This is all to say I've had some experience with multiple boats, and frankly, being overwhelmed by boat issues. The kind of trouble you're in now is pretty exciting, but that really depends on where you are in life and how enthusiastic you are. Boats can be not only a commitment, but also a liability. Depending on your skill level for doing repairs and maintenance, and what you are doing for storage, they can be quite expensive. Here's what I would do...

Step 1 - Prepare to spend a little money. You are now responsible for two boats. The development of your reputation in the boating community has begun. If this is something you're pretty sure you want to pursue for a hobby, keep in mind that this community can be pretty important to you. Ok, so figure out what you're dealing with. Can the boats hold water? Don't try to put them in the water if you're not 94,6 percent sure. If you do, ask the lift driver to let the boat(s) hang in the straps for a bit so you can assess (be sure to pull all of the cushions and removable interior bits before you do this. You want to see as much of the hull as possible before the boat goes into the water). While on the hard, Inspect the hulls and through hulls for issues. My recommendation is to find someone who knows boats that you can trust to accompany you, paid or not. Check for slop on the prop on the Newport (I'm assuming it has an inboard). This would indicate loose or missing packing around the prop shaft and will cause a leak. Topside holes are easy to patch and can wait until you figure out what you're doing. Figure out what tools/supplies you might need on hand for the coming week and get them to the boats.

Step 2 - Find a home for them. It's pretty clear that you have to move them, but it may be worth visiting the harbor master to see if you can rent a slip by showing that you're committed to getting one or both boats sailing. Alternatively, and maybe cheaper, you can find someone with a trailer to pull the boats to new destinations, whether they be your backyard or a boat yard. 5 Days isn't much time bit if you work with the powers that be and they know you are really trying to get them out, they may offer you a bit of grace. Either way, you're going to learn a bunch in the next 5 days...and probably stress the f*ck out. Unless you can get rid of one/both where they sit, they are your responsibility - Your new babies.... BTW, having kids prepares you for owning boats but ruins the possibility of using them at the same time. If you don't have kids and are really interested in trying this out, COMMIT - There's no better time in life.

Steps 3... Figure out how you're going to move them to the places you have set up for them to reside.

I could go on and on, but I've gotta go. Regardless of how it turns out - Good luck! While you've probably bitten off more than you can chew, this is an opportunity for growth and learning that will not likely come around again.